John Hackerson – Experienced Finance and Operations Executive

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John Hackerson is an accomplished investor-operator and business leader with approximately two decades of professional experience spanning operating leadership, private investment, investment banking, technology, business development, and military service. His career has been defined by an ability to move comfortably between strategy and execution—evaluating opportunities at the transaction level while also understanding what it takes to build teams, serve customers, improve margins, and operate businesses day to day. With experience across the full investment lifecycle, John has evaluated hundreds of acquisition targets, negotiated and structured transactions, led businesses following acquisition, and ultimately participated in successful exits. His leadership philosophy is grounded in accountability, disciplined decision-making, adaptability, and the belief that sustainable value is created through strong people and sound operating fundamentals.

John’s most significant operating experience has been concentrated in construction, landscaping, hardscaping, tree services, and other home-service businesses. As President of Scapes of North Florida, he helped transform a $1.5 million landscaping and hardscaping company into an approximately $8 million enterprise. During his tenure, he introduced a comprehensive digital marketing strategy that contributed to residential revenue growth of more than 260 percent over three years, established a commercial sales capability, and expanded the company’s geographic presence into Orlando. He also helped scale the organization from eight employees to more than 45, building field crews, estimating capabilities, and an operations management layer capable of supporting a larger, multi-market organization.

His work at Scapes demonstrates John’s ability to combine growth with operational discipline. Rather than viewing revenue expansion as an end in itself, he implemented structured budgeting and job-level financial reporting to provide greater visibility into performance, unit economics, and profitability. He redesigned hiring and onboarding processes to support expansion in a competitive labor environment and developed an AI-powered job-costing agent that allocated daily field labor hours by project. This capability enabled systematic post-project profitability analysis and illustrates a recurring theme throughout John’s career: applying analytical thinking and practical technology to solve real operating problems.

John simultaneously served as President of First Coast Pavers, a specialized paver installation and repair company acquired as a bolt-on to the Scapes platform. Under the broader operating strategy, the company expanded its commercial reach to property managers and general contractors while reducing its dependence on seasonal residential demand. A comprehensive brand and digital marketing overhaul contributed to approximately 385 percent revenue growth over four years. Scapes and First Coast Pavers were ultimately exited as part of a combined portfolio sale, with Scapes generating a reported 5.4x multiple on invested capital and 58.2 percent internal rate of return, while First Coast Pavers generated a reported 4.3x multiple and 52.9 percent internal rate of return.

Earlier, John served as President of Treeco, a tree trimming and removal services company in St. Augustine, Florida. Following the acquisition, he assumed responsibility for sales, marketing, finance, workforce management, and overall operations as the company’s principal executive. He expanded the business from a residential-only model into commercial tree services, improving revenue diversification and reducing seasonal cash-flow volatility. Through improvements in estimating, scheduling, crew utilization, and organic growth initiatives, Treeco doubled revenue during a 24-month hold period before its exit. John subsequently remained involved as a board member, adding formal governance experience to the perspective he had already developed as an operator.

Across these portfolio companies, John helped grow combined revenue from approximately $3.8 million at acquisition to $15.7 million at exit. That progression reflects his expertise in operational management, marketing, unit margins, profitability, commercial growth, team building, and P&L ownership. It also gives him a particularly relevant perspective for founders, investors, and boards navigating the challenges of scaling smaller and middle-market businesses. John understands that growth in resource-constrained environments requires more than a strategic plan; it requires leaders who can prioritize effectively, establish repeatable processes, develop talent, measure performance, and remain close enough to operations to recognize problems before they become structural.

Before becoming a portfolio-company operator, John developed leadership experience across technology and high-growth commercial environments. As Vice President of Market Operations and Business Development for the Southeast at Veryable, a labor marketplace technology platform, he held regional P&L responsibility and managed a team of 23 account executives and sales development representatives across multiple locations. During his tenure, Southeast regional monthly revenue grew from more than $120,000 to more than $610,000, representing approximately fivefold year-over-year growth. He also personally closed major enterprise relationships, demonstrating an ability to combine organizational leadership with direct commercial execution.

John’s experience at Zuora further broadened his perspective on executive leadership and organizational strategy. Serving as Chief of Staff to the CEO, he coordinated between the CEO’s office and functional teams to support key initiatives spanning product, sales, operations, and other areas of the business. He also developed a predictive analytics engine for the company’s sales pipeline designed to improve the assessment of deal probability and size and support more accurate forecasting following the company’s public offering. The role placed John at the intersection of executive decision-making, cross-functional execution, analytics, and organizational alignment—experience that continues to inform how he evaluates businesses and leadership teams.

His financial foundation was developed through investment banking roles at Morgan Stanley and Barclays Investment Bank. At Morgan Stanley, John worked in the Healthcare Group, supporting complex mergers and acquisitions, divestitures, and capital-raising assignments across medical technology and biotechnology. His transaction experience included the execution of a $172 million convertible bond offering for Nevro Corp., as well as strategic defense and follow-on equity assignments. At Barclays, he worked in the Natural Resources Group, where he evaluated substantial investments in distressed oil and gas debt and performed strategic alternatives and valuation analyses for energy companies. Earlier at Barclays, he developed multifactor operational risk models designed to assess the firm’s exposure to disruptive events and inform risk-mitigation decisions presented to senior management.

John’s approach to leadership was shaped well before his career in finance and business. He served in the United States Marine Corps as a Sergeant and Senior NCOIC of Armory Operations, overseeing 23 Marines during operations and humanitarian missions. He carried responsibility for personnel conduct, well-being, and combat readiness and earned two accelerated promotions—Combat Meritorious Corporal and Meritorious Sergeant—approximately a year ahead of his peers. His military experience also included gathering information during operations, synthesizing findings, and preparing concise after-action reports for senior officers. The experience instilled a lasting appreciation for accountability, preparation, composure, teamwork, and the responsibility leaders have to the people entrusted to them.

John complemented his practical leadership experience with a rigorous academic foundation. He earned his Master of Business Administration from the University of Chicago Booth School of Business and completed his undergraduate business education at the University of Virginia’s McIntire School of Commerce, with a background in commerce, finance, and international business. He has also held Series 79 and Series 63 credentials. Together, his education, financial training, transaction experience, and direct operating record allow him to approach business questions through multiple lenses: investor, banker, executive, operator, salesperson, team builder, and board member.

As a prospective board and advisory leader, John is particularly interested in construction, home services, and labor-related businesses, where his operating experience can translate directly into practical guidance. He is open to organizations at different stages and sizes, including businesses with fewer than 100 employees, and brings particular value to companies confronting questions around profitable growth, professionalization, commercial expansion, operational infrastructure, talent, acquisition integration, and eventual exit planning. His background allows him to understand both sides of the boardroom conversation: what investors need from a business and what operators must actually do to deliver those results.

John’s candidacy is distinguished by the breadth of the investment lifecycle he has personally experienced. He has evaluated acquisition opportunities, negotiated and structured transactions, taken direct responsibility for acquired companies, managed P&Ls, built teams, developed sales channels, implemented technology and reporting systems, and led businesses toward successful exits. This combination enables him to challenge assumptions without losing sight of operating realities. He can engage deeply with financial performance and transaction strategy while remaining equally attentive to customer acquisition, workforce development, execution discipline, organizational design, and the unit-level economics that ultimately determine whether a strategy succeeds.

Outside the boardroom, John maintains an adventurous and disciplined outlook. His interests include scuba diving, where he has achieved Rescue Diver experience,  as well as cross-country skiing and kite surfing at the novice level. He is open to travel and to expanding his international business exposure. These pursuits reflect qualities visible throughout his professional journey: curiosity, preparation, resilience, willingness to enter unfamiliar environments, and a continued desire to learn.

John Hackerson ultimately brings the perspective of a leader who has operated across remarkably different environments—from the United States Marine Corps and global investment banks to public technology companies and hands-on home-service businesses. The common thread is disciplined execution. His experience demonstrates that meaningful value creation occurs when strategic thinking is connected to operational accountability, financial insight is translated into practical action, and ambitious growth is supported by capable teams and sustainable economics. For boards seeking an executive who understands transactions as well as operations—and who can connect high-level strategy with what happens in the field—John offers a distinctive and highly practical perspective.

Character:
John exemplifies character through a career grounded in accountability, service, resilience, and responsibility for both people and results. From leading Marines to assuming direct responsibility for acquired businesses, he has consistently worked in environments where credibility is earned through preparation, sound judgment, and follow-through.

Knowledge:
He combines investment banking expertise, MBA-level financial training, transaction experience, commercial leadership, and firsthand P&L ownership with deep practical knowledge of construction and home-service operations. His ability to understand valuation, unit economics, marketing, workforce management, technology, and operational performance gives him a multidimensional perspective on value creation.

Strategic:
John approaches strategy as a bridge between opportunity and execution, identifying ways to diversify revenue, enter new markets, strengthen commercial capabilities, improve profitability, and build organizations capable of supporting growth. His experience across acquisitions, portfolio-company operations, scaling, and exits enables him to evaluate strategic decisions through both an investor’s and an operator’s lens.

Communication:
Communicating across environments ranging from military operations and field teams to senior executives, investors, bankers, customers, and corporate leadership. His background requires him to translate complex financial and strategic issues into actionable priorities while aligning people around clear objectives and measurable outcomes.

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Kacey Card
Kacey Cardhttps://boardsi.com
Kacey Card is an accomplished editor at Leadafi, bringing a keen eye for detail and a passion for storytelling to the team. He holds a Bachelor of Arts in Communication and Media Studies from the University of Hawaii at Manoa, where he graduated with a 3.8 GPA. Kacey has honed his skills in content creation, editing, and digital media, ensuring that every piece of content meets the highest standards of quality and engagement. At Leadafi, he is dedicated to crafting compelling narratives that resonate with readers and drive the publication's mission forward. His commitment to excellence and innovative approach to editing make him an invaluable asset to the team.